Jennifer Lopez and Diddy relationship timeline explored as former Bad Boy Ent. intern claims rap mogul sent his staff to win back JLO after breakup

On Tuesday, May 28, Rolling Stone published an exposé that put Diddy under blast. The elaborate story featured testimonials from multiple former friends, coworkers, and classmates. It also shed light on his relationship with fellow singer and ex-girlfriend Jennifer Lopez. It was alleged that Sean “Diddy” Combs did his best to intimidate women who attempted to “walk away” from their relationship.

Jennifer Lopez and Diddy began their relationship in 1999, when they were at the peak of their respective careers. Their paths first crossed when the former appeared as a princess in the latter’s Been Around the World music video. Following that, Combs worked with Lopez as a producer on her debut album.

Combs famously accompanied Lopez to the Grammy Awards in 2000, but the couple later called it quits in 2001. However, witnesses to their relationship now claim that Combs had a hard time letting their relationship go following their breakup.

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According to Rolling Stone, Combs had multiple Bad Boy Entertainment staff members stand outside the Total Request Live studio, where Lopez was shooting an MTV show alongside Matthew McConaughey. It was reported that the organization's employees held up sign cards in attempts for Combs to win back Lopez.

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Inside Jennifer Lopez and Diddy’s relationship as former Bad Boy Entertainment intern claims latter’s girlfriends were not allowed to walk away

Rolling Stone revealed in their latest Sean Combs story that the rap mogul did not make it clear to his partners that they were not allowed to leave their relationship. Damien Vasquez, a former intern at Bad Boy Entertainment, also told the publication that this was the reason why Diddy had multiple staffers camping outside the TRL studio.

Prior to their relationship coming to an end, Jennifer Lopez, Combs, the latter’s bodyguard Anthony Jones, and rapper Jamal “Shyne” Barrow were arrested after getting into a heated argument in a New York City club. The men faced charges; however, Lopez’s charges were dropped after law enforcement found a stolen gun in Lopez’s car following the incident.

Jennifer Lopez has since opened up about her relationship with Combs. In an interview with Vibe in 2003, she claimed that she never found Combs cheating, but she “knew” that he did. The On the Floor singer explained:

“He’d say he was going to a club for a couple of hours and then never come back that night. It was the first time I was with someone who wasn’t faithful."

However, in a 2015 interview with The Breakfast Club, Diddy said that the cheating should not come as a surprise to his partners. He stated on the radio show:

“If I’m in a relationship with you, 25 percent of your time, you’re gonna just feel like, ‘Aw, man, I hate being here, this guy cheated on me, he lied on me.’ But then there’s 75 percent of the time I’ma make you the happiest woman in the whole wide world. I’ma be there to support your dreams. I’ma be there to hold you, listen to you. I’ma be there to be your best friend."

Diddy’s former girlfriend, Cassie Ventura, also opened up about the singer’s actions following one of their initial breakups. Ventura, who filed a lawsuit against Combs in November, revealed that Combs’ “network of operatives found her and implored her to return,” with a Bad Boy Executive also threatening “to withhold the release of her music if she didn’t return.”

Speaking about Ventura and Combs’ relationship, an unnamed witness told Rolling Stone that Combs would often attempt to act like “a heartbroken, hurt man,” when he was “a liar [and] abuser” in reality.

Analyzing Diddy’s behavior, former Bad Boy president Kirk Burrowes told Rolling Stone that the murder of Diddy’s father left the rapper with “abandonment” issues, subsequently leading to women becoming victims of the issues.